Dating Multiple People (and Why You Should Be Doing It)

Finding a person that you mesh well with can take time. Depending on how you date, it can take a very long time.

When I first started online dating, I had this notion that dating more than one person simultaneously would somehow be insincere. I did my best to only talk to one girl at a time. There were times where I would end up talking to a few girls at once but this was always accidental.

With this approach, I went on one first-date every month, sometimes less. All of these dates were very stressful because of the time being I devoted just to get to the date. First date failure, whether because she wasn’t what I was looking for or the reverse, was very difficult. It always felt like starting all over and was always painful. Once I even continued to date a girl just to avoid “starting over”.

Reasons to Date Multiple People at Once

Around the eighth month of my online dating experience, I gave up on my “sincere” method of meeting girls and intentionally tried to meet as many girls as possible at once.

For the first few weeks, things were similar to my old method and I didn’t see immediate improvements but over time my dating life changed dramatically. I moved from one date a month to one a week and eventually was going on up to two first-dates a week.

There were several side-effects to this, aside from a busier schedule, that make me now believe this is the best way to approach online dating:

1. Better Definition

As I went on more and more dates in a short time period, I realized that what I really wanted in a woman and what I had been willing to accept were very different.

When I was only meeting one girl a month, there were so many qualities that I didn’t like that I would ignore simply because I didn’t want to have to start all over with someone else. I would continue to date someone negative or rude or conceited and would just hope that things would just eventually “work themselves out”.

All this changed when my dating schedule became very active. Breaking off communication with someone I had nothing in common with, or at least who was missing qualities I was looking for, became easy. Honestly, it was often a relief because there were more first dates waiting and I would be able to remove someone from my list of potentials.

This freedom allowed me to finally be honest with myself about what I was looking for. I stopped defending the poor qualities my dates had and started moving on. Dating in numbers allowed me to make decisions based on what I desired, not based on how lonely I was at that time. It also helped me better define what I was looking for in my profile.

2. Greater Comfort
One great side-effect to dating so actively was that I became more comfortable with dating itself. I was discovering which conversations worked better than others and was able to avoid bumps in the conversation all together.

The confusion of first-dates was disappearing altogether. I actually started to have fun. I hadn’t even thought that having fun could be a part of online dating but as I grew more comfortable, I had more fun. I still wasn’t the most confident guy (for example, I still wasn’t randomly asking girls out in public) but I was becoming very comfortable on dates, which gave the appearance of confidence.

3. Less Stress
With dating multiple women, there was always another first date on the horizon. Failure wasn’t so horrible any longer. I lost my hell-bent desire to make every date go perfectly.

When the stress lessened, I stopped paying attention to myself and started paying attention to my date. On one occasion when things were going very poorly, instead of stressing out, I told my date I didn’t think we were a great match but that we could still have fun over dinner. She seemed relieved and agreed to try to enjoy the dinner. We did have a nice time that evening and then proceeded to never speak to each other again.

Failure became a part of dating, neither good nor bad; just a part that has to be accepted.

4. Better First Impressions
This was a direct result of having less stress. As the stress began to lessen, I started representing who I was much better.

Early on I was always in a panic-mode: trying to make sure everything went perfect on every date, overly concerned about the happiness of my date, worried about the impression I was making and so on. Looking back, this only made my dates uncomfortable and left me looking either weird or desperate.

When I had multiple dates lined up, I found myself very relaxed on each date. Once I relaxed, I felt much better about the impressions I was leaving. Even when things didn’t work out and my date was not interested in seeing me again, at least I knew we just weren’t a match instead of wondering if I had only done “better” would she have liked me? When I was relaxed, there was no “doing better” or “doing worse”. There was only who I am.

5. Improved Odds
If you believe that you can get along with anyone out there then dating few people could work for you. For the rest of us, the biggest part of find that special someone is opportunity.

To put it another way: imagine there is a room with 100 singles of the opposite sex in it and in this imaginary room there is one person who is a “match” to you. Using my original method for dating (one girl a month at best), my odds of meeting that special someone were very low and theoretically it would have taken a very long time to meet her. Odds are years and years of dating.

The issue here is the length of time only identifies part of the problem as it assumes that the “match” won’t move on to something else: a new job that she wouldn’t have been taken had she been in a relationship, settling for someone just to not be alone, etc. Taking too long doesn’t just mean you’re looking longer. It can mean missing opportunities altogether.

I believe that dating many people improves your chances in two ways: you have a better chance of meeting someone who you are looking for but you also potentially avoid missing out on someone who may move on if you never get around to meeting in the first place.

Let’s take the example to the odds example to the other extreme: imagine that after a maximum of five dates everyone meets their special someone, guaranteed. Some may meet on the first date, some may meet on the third but no one ever needs to go beyond a fifth date.

Living in this imaginary world my question is this: how quickly would you go on your five dates? Would you attempt to meet your special someone sooner or later? If later, why date online at all? You’re risking meeting that special someone before the time you’ve appointed “appropriate”. If sooner, why wait by going on few dates? It seems logical that most people would go on their five dates as quickly as possible when desiring a relationship. I think the real world is similar, if not so simple!

6. Get Your Money’s Worth
If you are using online dating, chances are you are paying something. When I was meeting one person a month, it cost me exactly the same as when I was meeting seven a month. Why not get your money’s worth and meet several people?

After dating in numbers the benefits are very clear to me. However, every time I have offered this advice to friends it has been rejected as “not for them”.

There seems to be a general aversion to this kind of dating. This is why I laid out all the benefits above: just in case the everyone else is just like my friends. Just give it a try. Date as many people as you possibly can without getting confused. For some of us, that might be three. Other may be able to date a dozen and keep everything straight. I had eight first dates planned once and found it was way too much for me (fortunately none of the dates ended with me confusing one girl for another!).

In the end, I found that five worked best for me.Sometimes you won’t be able to date a lot of girls at one time. There may not even be two people you’re interested in with the service you use! If this is the case, chances are you are too picky so try to be open-minded. Take a few risks – ask out a few no-picture profiles. Yes, you’ll be living on the edge and, yes, you may not be attracted but at least you’ll be out there.

If all else fails, sign up for a second service somewhere or at least check out the members. In the case where you are contacting people but getting fewer responses than you would like, understand that it takes time. It took around five weeks from when I decided to date multiple girls to when I actually was dating multiple girls. It takes a little guess work but you should be contacting people until you feel that you are at your max for dating-without-confusion. When you remove someone from your list of potentials, start contacting people to fill that spot. This is tricky so be careful: play your cards wrong and you may find yourself with an empty list of potential dates or a list so large you can’t handle it!

Amen. I try to preach the virtues of this to my friends and I get the same response. What is amazing is some will quit altogether rather than try this. They think it’s immoral or something, when in reality, it simply is not whatsoever. It’s only wrong to lie to a girl and say you are not seeing anyone else, or getting intimate with multiple women and not telling them about the others, but you should be avoiding those things, not dating more than one person.

I also recommend that when people finally do set up a date, they go and message a few more people. Before dates, feel free to message another girl or two, just to help keep things in perspective.

Thanks for the guide, man. In my opinion, online dating is actually the ideal way to date and meet people. It’s way easier than in asking out strangers, and if you’re looking for something special, say, a Christian girl, that can be real tough, even at church, but online there are hundreds of girls looking for a Christian guy too. I had met a woman online years ago and got engaged, but it didn’t work out after a few years, so I’m getting back in the game and this website has helped me get my “skills” back.

Thanks Jason. I do think in general more and more people are coming around to the idea of online dating. As for dating many people at once…well, we are probably still in the minority there (or maybe not…perhaps most of the people who contact me for advice just aren’t doing it!).

And I do think you’re right: many people incorrectly look at it as a moral issue. On the other hand, I think some people just see dating multiple people as…well…not very romantic. They want magic sparks even before the first date which is a tall order and often a great time waster.

As I love to say, seems that too many people are looking for the perfect person so they can then date them instead of dating many people so they can find the perfect person. To each their own but I’m convinced the latter works better.

VJanuary 20, 2012

I wish there were instructions on how to say goodbye when you chose another person but still have feelings for the person you were dating.

ShayJanuary 25, 2012

Hi — Thanks for this post. I’ve been using an online dating site for a little over a month and have gotten 3 dates out of it so far and am chatting with a few other folks to see if those result in dates. I felt that two out of the three folks I dated would be better friends, but with one of the guys, I am definitely interested and want to see where it goes. My question is — in your experience, have you noticed that if you liked someone that that colored your opinion of people you went out with after the person you really felt a connection with? And, how many dates before you know that it’s just not a match? I have heard stories where people didn’t really click at first, but then things changed, so I’m just trying to get some feedback on not saying “no thanks” to people too prematurely. Thanks for any input you can provide.

Hi Shay – I absolutely found that making a connection with someone colored my opinion of other people and I think that’s fine. If you find someone great, other people are likely to become far less interesting.

I tried to go on 2 dates with everyone I met (well, later on in my online dating life at least). I did this because some people were much more comfortable after the first date was over and I felt like I got a better idea of who they really were. If there’s wasn’t a connection after 2 dates, I didn’t take it further than that but I don’t think there’s a hard and fast rule on that. You’d just want to be careful: if you don’t like them but continue to go on dates it can send the wrong message.

You will probably want to experiment and see what you’re most comfortable with but for me, 2 dates felt right.

EPearceMay 20, 2012

Do you have any statistics on how many women the guy needs to contact (on average) to get a coffee date? And how many coffee dates to get to a second and third date.

I know a guy kept a spreadsheet for six months on his dating experience. He said it took 25 contacts to get to coffee, then five coffees to get to second date and five second dates to get to a third.

EPearce – I have my own experience and the experiences that readers have shared, but no statistics for a large group of people. I think early on, my experience was similar to what the guy you mention described, however, once I started to get really comfortable with online dating it improved a lot.

I think at the end I was generally contacting between 5 and 10 women a week and was normally going on 2 first dates a week. I’d say about one in three dates went to a second date. However, with all those numbers keep in mind that I was much more open about who I dated than many people are and I went out of my way to give people a second chance and would often ask for a second date even when the first one wasn’t great. I think some people would look at my numbers/success and think that it’s impossible, but the trick is that my approach was much more accepting than what many others use.

PeterJune 12, 2012

Very interesting article.
I have just started, multiple dating, and it seems to work okay for me. Met some intersting women and cant say ive ever had a bad date, even if there was no way i was going to see her again.
I guess my fear is, by dating 2 per week (which is what i have been doing, wouldnt do anymore) at what point do you stop. How do you know that say no5 is the one, of youre already dating no 18 say?

Peter – I think it comes down to a personal decision and understanding yourself. In a certain sense, you may never “know” when you’ve met the one but hopefully you can recognize that you’ve met someone great enough to take the risk of ending communication with other people.

After my first date with the woman who became my wife, I got home and canceled something like 5 or 6 dates I had planned with other women. That was a big risk because if I was wrong about the connection I felt with Kate then I’d have to start over. However, I decided that it was worth the risk.

So unfortunately I don’t think I can offer advice that’s going to remove all the risk of recognizing “the one” but I would encourage you to be willing to take those risks when you think you might have found her. Maybe not immediately cancel your other dates like I did. Maybe it’s just that you stop looking to find new first dates. Whatever it is, if we never take that risk we could end up dating indefinitely!

PatrickAugust 13, 2012

I believe in multiple dating because I am finding most dates are bad in one way or another – examples: move too fast in romance / sex, drastically late, pulls a no show, or just no spark for either of us or both. I look at as part of the process and necessary to date multiple people to find the best match you can.

But my only issue is whether or not I should disclose that I am dating multiple people. Do you tell them? Or do you disclose that only when asked? While I am not doing anything that I should feel guilty over, I do know people get easily jealous. I would be fine if I knew my dates were doing the same provided they don’t talk much about their other dates – out of respect. If a date of mine chooses someone else over me, that’s just a sign that they were a better match to begin with and frees me up to find someone better for me too.

Then again, maybe jealousy rearing it’s ugly head is a good thing because it could be an indicator of future problems?

Generally I would discuss it on the first date. I wouldn’t just come out and say, “I’m dating multiple people”. I’d start the conversation by asking her how her online dating was going and then we’d share some of our horror stories and generally have a good laugh. Around this point I’d explain my logic on dating multiple people and I wanted her to be aware that I was doing so. No one ever got upset when I explain how I saw things (or at least they never showed it!)

I think one exception might be if we weren’t getting on very well or if I knew I didn’t have a lot of interest. At that point, I’m not sure it’s worth trying to work into the conversation.

I don’t think I’d worry to much about jealousy as an indicator but that’s just me. I think that early on I’d try to give the benefit of the doubt.

DaveSeptember 11, 2012

Well apparently this advice is meant solely for those who are swimming in cash. 2 or 3 dates a WEEK? What person who doesnt drive a BMW can afford that?

Dave – there’s nothing wrong with meeting at a coffee shop or a park for a first date. In the beginning, I thought a first date had to be something like dinner/movie and if I’d stuck with that thinking then, yes, that wouldn’t have been possible for me financially. I found the important part was meeting and spending some time together, not where we met or how much was spent on the first date.

PhilNovember 10, 2012

This is sound advice, I have no doubt about that. I only think your still shooting too low. I started this online dating game about 8 days ago. And have been on 6 dates so far. I even organised 3 dates in one day, one at 3pm, one quickie at 6pm (we agreed just 30 mins before hand) and one at 7pm.

This method of dating makes you very relaxed about the whole thing, basically ambivalent. Id suggest trying this style of online dating to anyone who lacks confidence with first dates or women in general. Its a sure fire method to bring you out of you shell. It will install the meh, whatever attitude in you.

One thing I would say though is pace yourself in terms of drinks. In fact id suggest maximum of 2 dates a day for this very reason. There is also the point of giving the date a chance to go somewhere, in my 3 dates day, only the last date of course was open ended, the other two were ending on schedule regardless.

But in my short OD experience, i think the first date should be viewed as more of a meeting generally, a meeting that can turn into a date sure, but an initial meeting nonetheless. Also in respect to a comment above, id say just be honest about dating multiple people, use the meeting excuse if you need one, the fact is, these are just tester dates, I told my ‘meeting’ that night that she was indeed the 3rd women I met that day, of course I said I saved the best for last etc etc, which was actually true, but I told her and she was fine with my explanation. If you are going on multiple dates with multiple women then its a different ball game, and I would either keep hush about that, or choose your words very carefully.

Set up lots of first dates and set them up quickly. Dont waste weekends on dates either, use mid week to set up your meetings if possible. Id also say avoid coffee dates (and dinners) unless you don’t drink, because I just got back from one of those and its been the worst yet, its daytime, its coffee, its very business like, it doesn’t leave much room for moving the date forwards. Go to a nice pub early evening, sit next to each other, as apposed to opposite each other.

The only downfall to this is money, its gonna add up fast I can see, even in the UK where i’m not going to be paying for the date, you still have to pay for yourself. A quick side note, on the 3 date day, all 3 would like a 2nd date, two of which I have set up, one is open ended, but she is just friend material in my eyes, so i’m not sure of the etiquette here. I also know im a bit of a dog, so friend may turn into sex and then ill have my morals eating at me, so think I may just sacrifice the friend potential on that one.

Date lots, date quick and your find someone im sure, at least im hopeful of it. I also just came out of a long term relationship, so meeting lots of women is simply a good experience to have, somewhat character building, somewhat of an ego boost and just plain fun.

Enjoy and try not to take these meetings too seriously.

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